In an interview with The Pulse of Radio regarding the album, Weiland stated: "It'll definitely be a sonic journey like the first album was, a little bit more focused since I'm not on a narcotic journey like I was on the last one. But, you know, still sort of all over the map, because my influences are so wide and varied." In an interview with MTV News, Weiland stated that the songs on "Happy" In Galoshes were inspired by the death of his brother, Michael (who also played drums on a song on the album), and Weiland's separation from his wife of eight years, Mary Forsberg.
"Happy" in Galoshes was originally reported to be a double album, but in actuality, it is a single album that is being offered in a deluxe edition.
On September 17, 2008, Spin.com posted an exclusive stream of "Paralysis", and the track "Missing Cleveland" was posted on Weiland's MySpace site. On October 24, Spin also posted another new song, "Crash". On October 27, rockdirt.com released the video for "Paralysis", which features actress Paz de la Huerta. On November 18, the album became available to preview on Scott Weiland's MySpace page. A series of 4 webisodes directed by Rocco Guarino were released on scottweiland.com to promote the single "Crash".
"Missing Cleveland" was the first single released from the album on November 11. On February 17, it was announced that fans could vote for the album's second single. The candidates for the voting are "Paralysis", "Blind Confusion", and "Killing Me Sweetly."
"Happy" in Galoshes debuted at #97 on the Billboard 200, selling 10,500 copies in its first week. The album received a 3.5/5 score from Rolling Stone magazine, and a four out of a possible five from Allmusic. Entertainment Weekly wasn't as approving, giving it a C- score.
October 11, 2008, Amazon.com listed the album on its website. The full track list was offered, including the title for the otherwise untitled track (track #13). The song "I Know It's Too Late" appears as a bonus track on the iTunes version of the album.